Substituent Effect on Catalytic Activities of [{η5-Ar4C4COC(O)Ar}Ru(CO)2Cl] in Racemization and DKR of Secondary Alcohols

The derivatives of [{η5‐Ph4C4COC(O)Ph}Ru(CO)2Cl] were synthesized to investigate the substituent effect of the ruthenium complexes on the racemization and the chemoenzymatic dynamic kinetic resolution (DKR) of secondary alcohols, in which the phenyl rings are substituted with several different grou...

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Bibliographic Details
Published in:ChemCatChem 2011-02, Vol.3 (2), p.354-359
Main Authors: Lee, Jin Hee, Kim, Namdu, Kim, Mahn-Joo, Park, Jaiwook
Format: Article
Language:English
Subjects:
dynamic kinetic resolution
electronic properties
enzymes
homogeneous catalysis
ruthenium
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Summary:The derivatives of [{η5‐Ph4C4COC(O)Ph}Ru(CO)2Cl] were synthesized to investigate the substituent effect of the ruthenium complexes on the racemization and the chemoenzymatic dynamic kinetic resolution (DKR) of secondary alcohols, in which the phenyl rings are substituted with several different groups. Derivatives with electron‐donating substituents showed better activities than those with electron‐deficient ones, both in the racemization and in the DKR. The ruthenium complex, [{η5‐Ar4C4COC(O)Ar}Ru(CO)2Cl] (Ar=4‐methoxyphenyl), showed an activity about 14 times higher than that of [{η5‐Ph4C4COC(O)Ph}Ru(CO)2Cl] in the racemization of 1‐phenylethanol. Glorious resolution: Substituent effects for the racemization and the dynamic kinetic resolution (DKR) of secondary alcohols are investigated by synthesizing derivatives of [{η5‐Ph4C4COC(O)Ph}Ru (CO)2Cl] with various substituents on the phenyl groups. Increasing the electron density of complexes leads to higher activity in the racemization and DKR.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201000304